The rearrangement of 1-thiophthalide was written by Prey, V.;Kerres, B.;Berbalk, H.. And the article was included in Monatshefte fuer Chemie in 1960.SDS of cas: 5388-42-1 This article mentions the following:
The rearrangement of the title compound (I) in the presence of primary, secondary, and tertiary bases, with or without pressure, was studied and a reaction scheme was proposed, and through conductivity, heat of combustion, and infrared measurement, the important intermediate stages for tertiary bases were identified. Thus, 2 g. I and 5 g. PhNH2 was heated in a sealed tube 3 hrs. at 190闂? and then about 0.1N HCl was added and a brown oil separated; this was crystallized from EtOH and then from H2O to give 1.65 g. 2-thiophthalide (II), m. 59-60闂? Some similar representative experiments with I were (reagent, molar ratio of reagent to I, temperature, time, product, m. p., % yield given): PhNH2, 1:5, 180闂? 1 hr., II, 60闂? quant.; PhNH2, 1:25, 190闂? 2 hrs., N-phenylphthalimide (III), 168闂? 92; PhNH2, 1:4 (sealed), room, 1 month, I, 116-17闂? 95; PhNH2, 1:4 (open), room, 1 week, III, 168闂? -; MePhNH, 1:1, 190闂? 3 hrs., I, -, 100; Et2PhN, 1:5, 190闂? 3 hrs., I, -, 100; o-ClC6H4NH2, 1:5, 190闂? 3 hrs., N-(o-chlorophenyl)phthalimide, 206闂? 86; p-ClC6H4NH2, 1:5, 190闂? 3 hrs., N-(p-chlorophenyl)phthalimide, 182-3闂? 96; o-toluidine, 1:5,190闂? 3 hrs., I,-, 100; BuNH2, 1:4, 190闂? 3 hrs., o,o’-bis(butylaminomethyl)benzoyl sulfide (IV), 181-2闂? about 5; aqueous NH3, -, 190闂? 3 hrs., diphthalyldiimide (V), 300闂? -; aqueous NH3, -, 240闂? 3 hrs., II, -, 40; aqueous NH3, -, reflux, 3 hrs., phthalide, 68-70闂? 50; pyridine, 1:5, about 100闂? 3 hrs., II,-, 100; quinoline, 1:5, 190闂? 3 hrs., II,-, 100; Et3N, 1:1, 190闂? 4 hrs., II,-, 97. IV when heated with H2O gave H2S, and the filtrate from IV when treated with concentrated HCl gave II. A solution of 2.4 g. NaHS and 5 g. phthalide was heated 3 hrs. at 200闂?and treated with concentrated HCl to give 3.5 g. dibenzyl sulfide-o,o’ dicarboxylic acid, m. 230-3闂? dibutylamide m. 244-6闂? The EtOH filtrate from V was concentrated and the residue was purified with tetrahydrofuran and C to give 21.7% II, m. 54-9闂? In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).
2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.SDS of cas: 5388-42-1
Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles